Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily-of-the-Valley Odorants Lilial and Bourgeonal
The silicon/germanium/tin analogues of the lily‐of‐the‐valley odorants lilial (rac‐1 a), compounds rac‐1 b, rac‐1 c, and rac‐1 d, and bourgeonal (2 a), compounds 2 b, 2 c, and 2 d, were synthesized and characterized for their olfactory properties, including GC–olfactometry studies. Compounds rac‐1 a...
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| Veröffentlicht in: | ChemPlusChem (Weinheim, Germany) Germany), 2014-12, Vol.79 (12), p.1747-1752 |
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| creator | Dörrich, Steffen Gelis, Lian Wolf, Steffen Sunderkötter, Astrid Mahler, Christoph Guschina, Elena Tacke, Reinhold Hatt, Hanns Kraft, Philip |
| description | The silicon/germanium/tin analogues of the lily‐of‐the‐valley odorants lilial (rac‐1 a), compounds rac‐1 b, rac‐1 c, and rac‐1 d, and bourgeonal (2 a), compounds 2 b, 2 c, and 2 d, were synthesized and characterized for their olfactory properties, including GC–olfactometry studies. Compounds rac‐1 a–c and 2 a–c possess a typical lily‐of‐the‐valley odor, whereas the stanna‐analogues rac‐1 d and 2 d, despite some floral aspects, clearly no longer belong to the lily‐of‐the‐valley family. In both series of the carbon/silicon/germanium/tin analogues studied, the lily‐of‐the‐valley odor decreases in the order of carbon |
| doi_str_mv | 10.1002/cplu.201402160 |
| format | Article |
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What's in a scent? Silicon/germanium/tin analogues of lilial and bourgeonal are synthesized and characterized for their olfactory properties (see scheme). A HEK293 cell line with stable expression of hOR17‐4 is used to analyze recombinant hOR17‐4 activation by the respective analogues. This C/Si/Ge/Sn switch strategy is a powerful tool to extend our knowledge of structure–odor correlations in the family of lily‐of‐the‐valley odorants.</description><identifier>ISSN: 2192-6506</identifier><identifier>EISSN: 2192-6506</identifier><identifier>DOI: 10.1002/cplu.201402160</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>bioisosterism ; germanium ; lily of the valley ; odorants ; silicon ; structure-activity relationships ; tin</subject><ispartof>ChemPlusChem (Weinheim, Germany), 2014-12, Vol.79 (12), p.1747-1752</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3270-7ae55e09157e4508d51ab27963927097f8cf4a27a8079cb23578499fe755e5de3</citedby><cites>FETCH-LOGICAL-c3270-7ae55e09157e4508d51ab27963927097f8cf4a27a8079cb23578499fe755e5de3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcplu.201402160$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcplu.201402160$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Dörrich, Steffen</creatorcontrib><creatorcontrib>Gelis, Lian</creatorcontrib><creatorcontrib>Wolf, Steffen</creatorcontrib><creatorcontrib>Sunderkötter, Astrid</creatorcontrib><creatorcontrib>Mahler, Christoph</creatorcontrib><creatorcontrib>Guschina, Elena</creatorcontrib><creatorcontrib>Tacke, Reinhold</creatorcontrib><creatorcontrib>Hatt, Hanns</creatorcontrib><creatorcontrib>Kraft, Philip</creatorcontrib><title>Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily-of-the-Valley Odorants Lilial and Bourgeonal</title><title>ChemPlusChem (Weinheim, Germany)</title><addtitle>ChemPlusChem</addtitle><description>The silicon/germanium/tin analogues of the lily‐of‐the‐valley odorants lilial (rac‐1 a), compounds rac‐1 b, rac‐1 c, and rac‐1 d, and bourgeonal (2 a), compounds 2 b, 2 c, and 2 d, were synthesized and characterized for their olfactory properties, including GC–olfactometry studies. Compounds rac‐1 a–c and 2 a–c possess a typical lily‐of‐the‐valley odor, whereas the stanna‐analogues rac‐1 d and 2 d, despite some floral aspects, clearly no longer belong to the lily‐of‐the‐valley family. In both series of the carbon/silicon/germanium/tin analogues studied, the lily‐of‐the‐valley odor decreases in the order of carbon<silicon<germanium<tin. A HEK293 cell line with stable tetracycline‐regulated expression of hOR17‐4 was generated to analyze recombinant hOR17‐4 activation by rac‐1 a–d and 2 a–d by using Ca2+ imaging. Bourgeonal (2 a) showed the highest activation potency, whereas lilial (rac‐1 a) and sila‐bourgeonal (2 b) exhibited lower activation potencies. Sila‐lilial (rac‐1 b), germa‐lilial (rac‐1 c), and stanna‐lilial (rac‐1 d), as well as germa‐bourgeonal (2 c) and stanna‐bourgeonal (2 d), did not activate heterologously expressed hOR17‐4 at the concentrations tested. The carbon/silicon/germanium/tin switch strategy thus showed that the stanna‐derivatives clearly exceeded the molecular dimensions of the odorant receptor(s) responsible for the recognition of lily‐of‐the‐valley odorants, although the receptor affinity was already affected with the sila‐ and germa‐analogues. These data could later be used in the qualitative and quantitative evaluation of computational receptor models.
What's in a scent? Silicon/germanium/tin analogues of lilial and bourgeonal are synthesized and characterized for their olfactory properties (see scheme). A HEK293 cell line with stable expression of hOR17‐4 is used to analyze recombinant hOR17‐4 activation by the respective analogues. This C/Si/Ge/Sn switch strategy is a powerful tool to extend our knowledge of structure–odor correlations in the family of lily‐of‐the‐valley odorants.</description><subject>bioisosterism</subject><subject>germanium</subject><subject>lily of the valley</subject><subject>odorants</subject><subject>silicon</subject><subject>structure-activity relationships</subject><subject>tin</subject><issn>2192-6506</issn><issn>2192-6506</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqF0EFPwyAYBmBiNHHRXT3zB7pRWko5bo2bxuqWuOmRsJZOlJYGWrX_wR9tt5llN7nwJS8PyfcCcOOjkY8QHme1bkcY-SHCfoTOwAD7DHsRQdH5yXwJhs69o_5EiGAaDMBPYspaWNGoTwknldCdUw6aAjZvEi50IbLG2A4uramlbZTcZ89Kq8xU47m0pahUW45Xqtprs23lkadKd54pvH72XoTWsoOL3FhRNW6XKaGhqHI4Na3dStPra3BRCO3k8O--AuvZ7Sq589LF_D6ZpF4WYIo8KiQhEjGfUBkSFOfEFxtMWRSwPma0iLMiFJiKGFGWbXBAaBwyVkjaM5LL4AqMDv9m1jhnZcFrq0phO-4jvquT7-rkxzp7wA7gS_Vb_POaJ8t0fWq9g1Wukd9HK-wHj2hACX99mvPZY0QJnT7wOPgFGGGJ4A</recordid><startdate>201412</startdate><enddate>201412</enddate><creator>Dörrich, Steffen</creator><creator>Gelis, Lian</creator><creator>Wolf, Steffen</creator><creator>Sunderkötter, Astrid</creator><creator>Mahler, Christoph</creator><creator>Guschina, Elena</creator><creator>Tacke, Reinhold</creator><creator>Hatt, Hanns</creator><creator>Kraft, Philip</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201412</creationdate><title>Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily-of-the-Valley Odorants Lilial and Bourgeonal</title><author>Dörrich, Steffen ; Gelis, Lian ; Wolf, Steffen ; Sunderkötter, Astrid ; Mahler, Christoph ; Guschina, Elena ; Tacke, Reinhold ; Hatt, Hanns ; Kraft, Philip</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3270-7ae55e09157e4508d51ab27963927097f8cf4a27a8079cb23578499fe755e5de3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>bioisosterism</topic><topic>germanium</topic><topic>lily of the valley</topic><topic>odorants</topic><topic>silicon</topic><topic>structure-activity relationships</topic><topic>tin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dörrich, Steffen</creatorcontrib><creatorcontrib>Gelis, Lian</creatorcontrib><creatorcontrib>Wolf, Steffen</creatorcontrib><creatorcontrib>Sunderkötter, Astrid</creatorcontrib><creatorcontrib>Mahler, Christoph</creatorcontrib><creatorcontrib>Guschina, Elena</creatorcontrib><creatorcontrib>Tacke, Reinhold</creatorcontrib><creatorcontrib>Hatt, Hanns</creatorcontrib><creatorcontrib>Kraft, Philip</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dörrich, Steffen</au><au>Gelis, Lian</au><au>Wolf, Steffen</au><au>Sunderkötter, Astrid</au><au>Mahler, Christoph</au><au>Guschina, Elena</au><au>Tacke, Reinhold</au><au>Hatt, Hanns</au><au>Kraft, Philip</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily-of-the-Valley Odorants Lilial and Bourgeonal</atitle><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle><addtitle>ChemPlusChem</addtitle><date>2014-12</date><risdate>2014</risdate><volume>79</volume><issue>12</issue><spage>1747</spage><epage>1752</epage><pages>1747-1752</pages><issn>2192-6506</issn><eissn>2192-6506</eissn><abstract>The silicon/germanium/tin analogues of the lily‐of‐the‐valley odorants lilial (rac‐1 a), compounds rac‐1 b, rac‐1 c, and rac‐1 d, and bourgeonal (2 a), compounds 2 b, 2 c, and 2 d, were synthesized and characterized for their olfactory properties, including GC–olfactometry studies. Compounds rac‐1 a–c and 2 a–c possess a typical lily‐of‐the‐valley odor, whereas the stanna‐analogues rac‐1 d and 2 d, despite some floral aspects, clearly no longer belong to the lily‐of‐the‐valley family. In both series of the carbon/silicon/germanium/tin analogues studied, the lily‐of‐the‐valley odor decreases in the order of carbon<silicon<germanium<tin. A HEK293 cell line with stable tetracycline‐regulated expression of hOR17‐4 was generated to analyze recombinant hOR17‐4 activation by rac‐1 a–d and 2 a–d by using Ca2+ imaging. Bourgeonal (2 a) showed the highest activation potency, whereas lilial (rac‐1 a) and sila‐bourgeonal (2 b) exhibited lower activation potencies. Sila‐lilial (rac‐1 b), germa‐lilial (rac‐1 c), and stanna‐lilial (rac‐1 d), as well as germa‐bourgeonal (2 c) and stanna‐bourgeonal (2 d), did not activate heterologously expressed hOR17‐4 at the concentrations tested. The carbon/silicon/germanium/tin switch strategy thus showed that the stanna‐derivatives clearly exceeded the molecular dimensions of the odorant receptor(s) responsible for the recognition of lily‐of‐the‐valley odorants, although the receptor affinity was already affected with the sila‐ and germa‐analogues. These data could later be used in the qualitative and quantitative evaluation of computational receptor models.
What's in a scent? Silicon/germanium/tin analogues of lilial and bourgeonal are synthesized and characterized for their olfactory properties (see scheme). A HEK293 cell line with stable expression of hOR17‐4 is used to analyze recombinant hOR17‐4 activation by the respective analogues. This C/Si/Ge/Sn switch strategy is a powerful tool to extend our knowledge of structure–odor correlations in the family of lily‐of‐the‐valley odorants.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/cplu.201402160</doi><tpages>6</tpages></addata></record> |
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| source | Wiley Journals |
| subjects | bioisosterism germanium lily of the valley odorants silicon structure-activity relationships tin |
| title | Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily-of-the-Valley Odorants Lilial and Bourgeonal |
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